Just start betting right on flop, he wont pay us anyways much unless he doesn't have a hand. You don't even have to bet it very big, make it like 1/2 or something similar. So you will be able to get his stack on river.

And if I am Checking behind on flop then I would likely consider throwing a small raise on turn.

Although that's true that sometimes I do pick such a line when I am against some smaller stacks while we can easily even over-shove and they might hit something like K or A.